Head of Ops

About Pickle

Pickle is a peer-to-peer rental marketplace unlocking the value of the billions of underutilized items sitting in consumers' closets. We make it easy to rent high-quality items exactly when you need them - with fast, convenient fulfillment and an on-demand experience that's as seamless as shopping.

We're building a new kind of commerce layer: one powered by dynamic local supply, where access is more convenient. Pickle is now live nationwide and scaling rapidly in key local markets including NYC, LA, and Miami. Our marketplace already features 300K+ items listed for rent, and we're just getting started.

What makes Pickle different is the combination of incredible peer-to-peer inventory, industry-leading convenience (under 2 days nationwide and under 2 hours locally), and an on-demand model with no subscriptions - users rent what they want, when they want it. Backed by our Series A funding raised in early 2025 from First Mark and Craft, we're scaling quickly and building the future of access-driven shopping.

About This Role

We're looking for a Head of Operations to design and build the next chapter of Pickle's operational backbone. You'll define the systems, partnerships, and pricing strategies that make our marketplace run-today and s person will own everything from last-mile delivery pricing to creative new exchange models like dry cleaner pickups, local hubs, or trusted community return partners.

As Head of Operations, you'll own Pickle's national logistics vision and its execution. You'll oversee all fulfillment, courier, and shipping networks; negotiate large-scale partnerships; and shape the unit economics that make our marketplace thrive. You'll experiment with new delivery methods and exchange channels-from neighborhood hub pilots to third-party repair and cleaning integrations-and ensure each is operationally sound and scalable.

You'll manage and mentor a growing operations team while working cross-functionally with Product and Data to build the tools and insights that power our operational excellence.

Requirements

• 8+ years of experience leading operations, logistics, or marketplace strategy (fashion, DTC, or last-mile delivery a plus)
• Experience working with dual-sided marketplaces
• Proven success building and scaling logistics networks across multiple cities or regions
• Deep experience with courier pricing, rate negotiation, and cost optimization
• Demonstrated ability to design operational systems and processes that scale efficiently
• Strong analytical background-comfortable with data modeling, forecasting, and decision-making using metrics
• Experience leading customer support or trust & safety functions within a consumer-facing platform
• Excellent collaborator, capable of working closely with Product, Eng, Marketing, and Community teams
• Entrepreneurial and creative mindset; excited to design new, unconventional exchange models
• Comfortable operating in a fast-paced, ambiguous startup environment
• Bonus: experience with 3PL integrations, hybrid logistics models, or localized operations playbooks

Responsibilities

• Define and lead Pickle's long-term logistics and operations strategy across all markets
• Build and manage nationwide partnerships with courier networks, shippers, repair partners, and local facilitators
• Design and implement scalable, cost-efficient delivery and return models
• Negotiate large-scale provider contracts and continually optimize pricing structures
• Launch pilots with new exchange methods (dry cleaners, community hubs, local ambassadors) and scale successful models nationally
• Develop operational data infrastructure and dashboards to track fulfillment speed, costs, and order success rates
• Partner with Product and Engineering to automate key workflows and improve delivery reliability
• Oversee Customer Experience and Trust & Safety alongside dedicated team leads
• Drive operational KPIs and report performance metrics to leadership, balancing speed, cost, and customer delight
• Mentor and develop the growing operations team; build a culture of ownership and creative problem solving

Benefits

• Competitive compensation and equity
• Healthcare (Medical, Dental, Vision)
• Take what you need paid time off
• Meal Pal credits to cover the cost of lunch
• Stipend to help set up your desk and office environment
• Work directly with the founders and executive team
• Professional coaching, training, and development
• Grow with the company
• Pickle credits for our employees, we love when the team uses Pickle!
• Fun team events and company parties
• Company offsites
• Office space in NYC